Involvement of CYP2D6 in the in vitro metabolism of amphetamine, two N-alkylamphetamines and their 4-methoxylated derivatives

References

• ALVAN, G., GRIND, M., GRAFFNER, C. and SJOQVIST, F., 1984, Relationship of N-demethylation of amiflamine and its metabolite to debrisoquine hydroxylation polymorphism. Clinical Phar-macology and Therapeutics, 36, 515–519.
   PubMed Web of Science ®Google Scholar
• BECKETT, A. H. and MIDHA, K. K., 1974, The identification of four metabolic products after incubation of p-methoxyamphetamine with liver preparations of various species. Xenobiotka, 4, 297-311. CALDWELL, J., 1976, The metabolism of amphetamines in mammals. Drug Metabolism Reviews, 5, 219–280.
   Google Scholar
• CHO, A. K., HIRAMATSU, M., DISTEFANO, E. W., CHANG, A. S. and JENDEN, D. J., 1990, Stereochemical differences in the metabolism of 3,4-methylenedioxymethamphetamine in vivo and in vitro: a pharmacokinetic analysis. Drug Metabolism and Disposition, 18, 686–691.
   PubMed Web of Science ®Google Scholar
• CHu, T., KUMAGAI, Y., DISTEFANO, E. W. and CH0, A. K., 1996, Disposition of methylene-dioxymethamphetamine and three metabolites in the brains of different rat strains and their possible roles in acute serotonin depletion. Biochemical Pharmacology, 51, 789–796.
   Google Scholar
• COLEMAN, T., ELLIS, S. W., MARTIN, I. J., LENNARD, M. S. and TUCKER, G. T., 1996, 1-Methy1-4-pheny1-1,2,3,6-tetrahydropyridine (MPTP) is N-demethylated by cytochromes P450 2D6, 1A2 and 3A4 — implications for susceptibility to Parkinson's disease. Journal of Pharmacology and Experimental Therapeutics, 277 685–690.
   PubMed Web of Science ®Google Scholar
• COUTTS, R. T., BACH, M. V. and BAKER, G. B., 1997, Metabolism of amitriptyline with CYP2D6 expressed in a human cell line. Xenobiotka, 27, 33–47.
   PubMed Web of Science ®Google Scholar
• COUTTS, R. T., BOLAJI, 0. 0., Su, P. and BAICER, G. B., 1994, Metabolism of methoxyphenamine in vitro by a CYP2D6 microsomal preparation. Drug Metabolism and Disposition, 22, 756–760.
   Google Scholar
• COUTTS, R. T. and DAWSON, G. W., 1977, Urinary excretion of phenolic metabolites of N-(n-propyl)amphetamine in man. Research Communications in Chemical Pathology and Pharmacology, 17, 349–352.
   PubMedGoogle Scholar
• COUTTS, R. T., DAWSON, G. W. and Jos, G. R., 1978, In vivo metabolism of N-alkylamphetamines in the rat — the effect of N-alkyl chain length on oxidation of the aromatic ring. Research Communications in Chemical Pathology and Pharmacology, 22, 589–592.
   PubMedGoogle Scholar
• COUTTS, R. T., DAWSON, G. W., KAZAKOFF, C. W. and WONG, J. Y., 1976, In vivo phenolic metabolites of N-alkylamphetamines in the rat. Evidence in favor of catechol formation. Drug Metabolism and Disposition, 4, 256–261.
   PubMed Web of Science ®Google Scholar
• COUTTS, R. T. and Jos, G. R., 1982, In vivo and in vitro 0-methylation of 1-(3,4-dihydroxypheny1)-2-(n-propyl-amino) propane, an intermediate in N-(n-propyl)amphetamine metabolism. Research Communications in Chemical Pathology and Pharmacology, 36, 173–176.
   PubMedGoogle Scholar
• DAHL, M. L., TYBRING, G., ELWIN, C. E., ALM, C., ANDREASSON, K., GYLLENPAL M. and BERTILSSON L., 1994, Stereoselective disposition of mianserin is related to debrisoquin hydroxylation polymorphism. Clinical Pharmacology and Therapeutics, 56, 176–183.
   Google Scholar
• DUNCAN, J. D., HALLSTROM, G., PAULSEN -SORMAN U., LINDEKE, B. and CH0, A. K., 1983, Effects of a-carbon substituents on the N-demethylation of N-methyl-2-phenethylamines by rat liver microsomes. Drug Metabolism and Disposition, 11, 15–20.
   Google Scholar
• GEERTSEN, S., FOSTER, B. C., WILSON, D. L., CYR, T. D. and CASLEY, W., 1995, Metabolism of methoxyphetamine and 2-methoxyamphetamine in P4502D6-transfected cells and cell preparations. Xenobiotka, 25, 895–906.
   PubMed Web of Science ®Google Scholar
• GORROD, J. W., 1973, The metabolism and excretion of 'amphetamines' in man. In Frontiers in Catecholamine Research edited by E. Usdin and S. H. Snyder (Oxford: Pergamon), pp. 945–950.
   Google Scholar
• GRACE, J. M., KINTER, M. T. and MACDONALD, T. L., 1994, Atypical metabolism of deprenyl and its enantiomer (S)-( +)-N,a-dimethyl-N-propynylphenethylamine, by cytochrome P450 2D6. Chemical Research in Toxicology, 7, 286–290.
   PubMed Web of Science ®Google Scholar
• HIRATSUKA, A., CHu, T. Y., DISTEFANO, E. W., LIN, L. Y., SCHMITZ, D. A. and CHO, AK., 1995, Inactivation of constitutive hepatic cytochromes P450 by phencyclidine in the rat. Drug Metabolism and Disposition, 23, 201–206.
   PubMed Web of Science ®Google Scholar
• KITCHEN, I., TREMBLAY, J., ANDRE, J., DRING, L. G., IDLE, J. R., SMITH, R. L. and WILLIAMS, R. T., 1979, Interindividual and interspecies variation in the metabolism of the hallucinogen 4-methoxyamphetamine. Xenobiotka, 9, 397–404.
   PubMed Web of Science ®Google Scholar
• KOBAYASHI, S., MURRAY, S., WATSON, D., SESARDIC, D., DAvws, D. S. and BOOBIS, A. R., 1989, The specificity of inhibition of debrisoquine 4-hydroxylase activity by quinidine and quinine in the rat is the inverse of that in man. Biochemical Pharmacology, 38, 2795–2799.
   PubMed Web of Science ®Google Scholar
• KUMAGAI, Y., LIN, L. Y., HIRATSUKA, A., NARIMATSU, S., SUZUKI, T., YAMADA, H., OGURI, K., YOSHIMURA, H. and CHO, A. K., 1994, Participation of cytochrome P450-2B and -2D isozymes in the demethylenation of methylenedioxymethamphetamine enantiomers by rats. Molecular Pharmacology, 45,359–365.
   Google Scholar
• LIN, L. Y., KUMAGAI, Y. and Cuo, A. K., 1992, Enzymatic and chemical demethylenation of (methylenedioxy)amphetamine and (methylenedioxy)methamphetamine by rat brain micro - somes. Chemical Research in Toxicology, 5,401–406.
   PubMed Web of Science ®Google Scholar
• MASUBUCHI, Y., HOSOKAWA, S., HORIE, T., SUZUKI, T., OHMORI, S., KITADA, M. and NARIMATSU, S., 1994, Cytochrome P450 isozymes involved in propranolol metabolism in human liver microsomes. The role of CYP2D6 as ring-hydroxylase and CYP1A2 as N-desisopropylase. Drug Metabolism and Disposition, 22, 909–915.
   PubMed Web of Science ®Google Scholar
• MIDI-IA, K. K., COOPER, J. K., BAILEY, K. and HUBBARD, J. W., 1981, The metabolism of 3-methoxyamphetamine in dog, monkey and man. Xenobiotica, 11, 137–146.
   Google Scholar
• NARIMATSU, S., MASUBUCHI, Y., HOSOKAWA, S., OHMORI, S., KITADA, M. and SUZUKI, T., 1994, Involvement of a cytochrome P4502D subfamily in human liver microsomal bunitrolol 4-hydroxylation. Biological and Pharmaceutical Bulletin, 17, 803–807.
   PubMed Web of Science ®Google Scholar
• NIELSEN, K. K., BROSEN, K., HANSEN, M. G. and GRAM, L. F., 1994, Single-dose kinetics of clomipramine: relationship to the sparteine and S-mephenytoin oxidation polymorphisms. Clinical and Pharmacological Therapeutics, 55,518–527.
   PubMed Web of Science ®Google Scholar
• ONO, S., TSUTSUI, M., GONZALEZ, F. J., SATOH, T., MASUBUCHI, Y., HOR1E, T., SUZUKI, T. and NARIMATSU, S., 1995, Oxidative metabolism of bunitrolol by complementary DNA-expressed human cytochrome P450 isozymes in a human hepatoma cell line (Hep G2) using recombinant vaccinia virus. Pharmacogenetics, 5 97–102.
   Google Scholar
• SHULGIN, A. T., SARGENT, T. and NARANJO, C., 1969, Structure—activity relationships of one-ring psychotomimetics. Nature, 221, 537–541.
   PubMed Web of Science ®Google Scholar
• SINDRUP, S. H., BROSEN, K., HANSEN, M. G., AAES-JORGENSEN, T., OVERO, K. F. and GRAM, L., 1993, Pharmacokinetics of citalopram in relation to the sparteine and the mephenytoin oxidation polymorphisms. Therapeutic Drug Monitoring, 15, 11–17.
   Google Scholar
• SMITH, R. L. and DRING, L. G., 1970, Patterns of metabolism of /3-phenylisopropylamines in man and other species. In E. Costa and S. Garattini (eds), Amphetamines and Related Compounds; Proceedings of the Mario Negri Institute of Pharmacological Research (New York: Raven), pp. 121–139.
   Google Scholar
• Su, PING, COUTTS, R. T., BAKER, G. B. and DANESHTALAB M., 1993, Analysis of imipramine and three metabolites produced by isozyme CYP2D6 expressed in a human cell line. Xenobiotka, 23, 1289–1298.
   Google Scholar
• TSENG, L. F., MENON, M. K. and Lou, H. H., 1976, Comparative actions of monomethoxy-amphetamines on the release and uptake of biogenic amines in brain tissue. Journal of Pharmacology and Experimental Therapeutics, 197, 263–271.
   PubMed Web of Science ®Google Scholar
• TUCKER, G. T., LENNARD, M. S., ELLIS, S. W., WOODS, H. F., CHO, A. K., LIN, L. Y., HIRATSUKA, A., SCHMITZ, D. A. and CHu, T. Y., 1994, The demethylenation of methylenedioxymeth-amphetamine ('ecstasy') by debrisoquine hydroxylase (CYP2D6). Biochemical Pharmacology, 47, 1151–1156.
   PubMed Web of Science ®Google Scholar
• WILLIAMS, R. T., CALDWELL, J. and DRING, L. G., 1973, Comparative metabolism of some amphetamines in various species. In Frontiers in Catecholamine Research, edited by E. Usdin and S. H. Snyder (Oxford: Pergamon), pp. 927–932.
   Google Scholar
• YASUI, N., OTANI, K., KANEKO, S., OHKUBO, T., OSANAI, T., ISHIDA, M., MIHARA, K., KONDO, T., SUGAWARA, K. and FuKusurvu,, Y., 1995, Inhibition of trazodone metabolism by thioridazine in humans. Therapeutic Drug Monitoring, 17, 333–335.
   Google Scholar